Hydrochloric Acid → HCID 58505684, compound

HRID 1917606Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[N:18]3[C:13]([CH:14]=[C:15]([O:19][CH2:20][C:21]4[CH:30]=[CH:29][C:28]5[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=5)[N:22]=4)[CH:16]=[CH:17]3)=[C:12]([C:31](=[O:37])[CH2:32][C:33]([CH3:36])([CH3:35])[CH3:34])[C:11]=2[CH2:38][C:39]([CH3:46])([CH3:45])[C:40]([O:42]CC)=[O:41])=[O:9])=[CH:4][CH:3]=1.[OH-].[Na+].Cl>C1COCC1.CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:10]2[N:18]3[C:13]([CH:14]=[C:15]([O:19][CH2:20][C:21]4[CH:30]=[CH:29][C:28]5[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=5)[N:22]=4)[CH:16]=[CH:17]3)=[C:12]([C:31](=[O:37])[CH2:32][C:33]([CH3:35])([CH3:36])[CH3:34])[C:11]=2[CH2:38][C:39]([CH3:46])([CH3:45])[C:40]([OH:42])=[O:41])=[O:9])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 23 °C

Procedure

A solution of ethyl 3-{3-[(4-chlorophenyl)carbonyl]-1-(3,3-dimethylbutanoyl)-7-(quinolin-2-ylmethoxy)indolizin-2-yl}-2,2-dimethylpropanoate (39 mg, 0.06 mmol) in THF (1 mL), MeOH (1 mL), and 6M aqueous NaOH (1 mL) is heated at 70° C. for 2.5 h then cooled to 23° C. and acidified to pH=1 with 6 M aqueous HCl. The mixture is partitioned between CH2Cl2 and brine then the organics are collected and dried with MgSO4, filtered, and concentrated in vacuo. The crude is purified by flash chromatography (SiO2, CH2Cl2 to 10% MeOH in CH2Cl2) to give the title compound (8 mg, 22%).

Workup

customThe mixture is partitioned between CH2Cl2 and brine
customthe organics are collected
dry with materialdried with MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude is purified by flash chromatography (SiO2, CH2Cl2 to 10% MeOH in CH2Cl2)

Sources & evidence

ORD record: ord-b85b289ba2f24a229e1e71e7bbc67f9c
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618300B2

Reaction notes

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